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5-Alkyl-1,2,3,4-tetrahydroquinolines

AlkaPlorer ID: AK031034

Synonym: 'gentamicin C1'

IUPAC Name: (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-[(1R)-1-(methylamino)ethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol

Structure

SMILES: CN[C@@H]1[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@H]([C@@H](C)NC)CC[C@H]3N)[C@@H](N)C[C@H]2N)OC[C@]1(C)O

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InChI: InChI=1S/C21H43N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3/t9-,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+/m1/s1

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InChIKey: CEAZRRDELHUEMR-CAMVTXANSA-N

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Reference

PubChem CID: 72395

CAS: 25876-10-2

SuperNatural Ⅲ: SN0043208-03

NPASS: NPC155631

Properties Information

Molecule Weight: 477.6030000000004

TPSA？: 199.73

MolLogP？: -3.327499999999995

Number of H-Donors: 8

Number of H-Acceptors: 12

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Acinetobacter baumannii Acinetobacter baumannii MIC 1000.0 nM 10.1021/acs.jmedchem.1c00614
Bacillus subtilis Bacillus subtilis DIZ nan None 10.1016/j.ejmech.2017.11.025
Bacillus subtilis Bacillus subtilis Kd 120000.0 nM 10.1016/j.bmcl.2005.02.007
Bacillus subtilis Bacillus subtilis MIC 18.0 ug.mL-1 10.1016/j.ejmech.2018.11.026
Bacillus subtilis Bacillus subtilis MIC 1000.0 nM 10.1021/acs.jmedchem.1c00614
Bacillus subtilis Bacillus subtilis MIC nan None 10.1016/j.bmcl.2019.06.031
Bacillus subtilis Bacillus subtilis MIC nan None 10.1021/acs.jnatprod.8b00321
Candida albicans Candida albicans DIZ nan None 10.1016/j.ejmech.2017.11.025
Candida albicans Candida albicans MIC nan None 10.1016/j.bmcl.2019.06.031
Candida parapsilosis Candida parapsilosis DIZ nan None 10.1016/j.ejmech.2017.11.025
Candida tropicalis Candida tropicalis DIZ nan None 10.1016/j.ejmech.2017.11.025
Citrobacter amalonaticus Citrobacter amalonaticus MIC 512.0 ug.mL-1 10.1039/d2md00459c
Enterobacter cloacae Enterobacter cloacae MIC 0.5 ug.mL-1 10.1021/jm00155a004
Enterobacter cloacae Enterobacter cloacae MIC 2.0 ug.mL-1 10.1021/jm00155a004
Enterobacter cloacae Enterobacter cloacae MIC 512.0 ug.mL-1 10.1039/d2md00459c
Enterococcus faecalis Enterococcus faecalis IZ 10.6 mm 10.1016/j.ejmech.2019.111892
Enterococcus faecalis Enterococcus faecalis MIC 4000.0 nM 10.1021/acs.jmedchem.1c00614
Escherichia coli Escherichia coli DIZ nan None 10.1016/j.ejmech.2017.11.025
Escherichia coli Escherichia coli IZ 25.4 mm 10.1039/d2md00192f
Escherichia coli Escherichia coli MIC 0.25 ug.mL-1 10.1021/jm00155a004
Escherichia coli Escherichia coli MIC 0.5 ug.mL-1 10.1016/j.bmcl.2006.09.007
Escherichia coli Escherichia coli MIC 0.5 ug.mL-1 10.1016/j.bmcl.2010.09.084
Escherichia coli Escherichia coli MIC 0.5 ug.mL-1 10.1021/jm00155a004
Escherichia coli Escherichia coli MIC 1.0 ug.mL-1 10.1016/j.bmcl.2010.09.084
Escherichia coli Escherichia coli MIC 3.0 ug.mL-1 10.1016/j.bmcl.2019.06.031
Escherichia coli Escherichia coli MIC 4.0 ug.mL-1 10.1016/j.bmcl.2010.09.084
Escherichia coli Escherichia coli MIC 5.0 ug.mL-1 10.1016/j.ejmech.2020.113034
Escherichia coli Escherichia coli MIC 16.0 ug.mL-1 10.1021/jm00155a004
Escherichia coli Escherichia coli MIC 32.0 ug.mL-1 10.1021/jm00155a004
Escherichia coli Escherichia coli MIC 63.0 ug.mL-1 10.1021/jm00155a004
Escherichia coli Escherichia coli MIC 64.0 ug.mL-1 10.1016/j.bmcl.2010.09.084
Escherichia coli Escherichia coli MIC 128.0 ug.mL-1 10.1016/j.bmcl.2010.09.084
Escherichia coli Escherichia coli MIC 256.0 ug.mL-1 10.1039/d2md00459c
Escherichia coli Escherichia coli MIC 512.0 ug.mL-1 10.1039/d2md00459c
Escherichia coli Escherichia coli MIC 4000.0 nM 10.1021/acs.jmedchem.1c00614
Escherichia coli Escherichia coli MIC=>80 0.99 ug ml-1 10.1021/acs.jmedchem.1c01551
Klebsiella aerogenes Klebsiella aerogenes MIC 512.0 ug.mL-1 10.1039/d2md00459c
Klebsiella oxytoca Klebsiella oxytoca DIZ nan None 10.1016/j.ejmech.2017.11.025
Klebsiella pneumoniae Klebsiella pneumoniae IZ 16.0 mm 10.1016/j.ejmech.2020.112832
Klebsiella pneumoniae Klebsiella pneumoniae IZ 26.3 mm 10.1016/j.ejmech.2017.10.046
Klebsiella pneumoniae Klebsiella pneumoniae MIC 0.03 ug.mL-1 10.1021/acs.jnatprod.2c00624
Klebsiella pneumoniae Klebsiella pneumoniae MIC 0.07 ug.mL-1 10.1021/acs.jnatprod.2c00624
Klebsiella pneumoniae Klebsiella pneumoniae MIC 0.24 ug.mL-1 10.1016/j.ejmech.2017.10.046
Klebsiella pneumoniae Klebsiella pneumoniae MIC 0.25 ug.mL-1 10.1021/jm00155a004
Klebsiella pneumoniae Klebsiella pneumoniae MIC 512.0 ug.mL-1 10.1039/d2md00459c
Klebsiella pneumoniae Klebsiella pneumoniae MIC 16000.0 nM 10.1021/acs.jmedchem.1c00614
Priestia megaterium Priestia megaterium MIC nan None 10.1016/j.bmcl.2019.06.031
Proteus mirabilis Proteus mirabilis MIC 1.0 ug.mL-1 10.1021/jm00155a004
Proteus vulgaris Proteus vulgaris IZ 23.4 mm 10.1016/j.ejmech.2017.10.046
Proteus vulgaris Proteus vulgaris MIC 1.95 ug.mL-1 10.1016/j.ejmech.2017.10.046
Providencia rettgeri Providencia rettgeri MIC 0.06 ug.mL-1 10.1021/jm00155a004
Providencia rettgeri Providencia rettgeri MIC 8.0 ug.mL-1 10.1021/jm00155a004
Providencia stuartii Providencia stuartii MIC 1.0 ug.mL-1 10.1021/jm00155a004
Providencia stuartii Providencia stuartii MIC 125.0 ug.mL-1 10.1021/jm00155a004
Pseudomonas aeruginosa Pseudomonas aeruginosa IZ 18.0 mm 10.1016/j.ejmech.2017.11.025
Pseudomonas aeruginosa Pseudomonas aeruginosa IZ 22.3 mm 10.1021/acsmedchemlett.2c00420
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 0.05 ug.mL-1 10.1021/acs.jnatprod.2c00624
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 0.25 ug.mL-1 10.1021/jm00155a004
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 0.5 ug.mL-1 10.1021/jm00155a004
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 1.0 ug.mL-1 10.1021/jm00155a004
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 2.0 ug.mL-1 10.1021/acs.jnatprod.8b00321
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 4.0 ug.mL-1 10.1016/j.bmcl.2006.09.007
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 4.0 ug.mL-1 10.1021/jm00155a004
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 16.0 ug.mL-1 10.1021/jm00155a004
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 125.0 ug.mL-1 10.1021/jm00155a004
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 128.0 ug.mL-1 10.1016/j.bmcl.2006.09.007
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 500.0 nM 10.1021/acs.jmedchem.1c00614
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 1630.0 nM 10.1021/acsmedchemlett.0c00425
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 4000.0 nM 10.1021/acs.jmedchem.1c00614
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 8000.0 nM 10.1021/acs.jmedchem.1c00614
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 17000.0 nM 10.1021/acs.jnatprod.7b00496
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 64000.0 nM 10.1021/acs.jmedchem.1c00614
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC=>80 7.94 ug ml-1 10.1021/acs.jmedchem.1c01551
Pseudomonas sp. Pseudomonas sp. MIC 6.0 ug.mL-1 10.1016/j.bmcl.2019.06.031
Salmonella enterica Salmonella enterica MIC 0.07 ug.mL-1 10.1021/acs.jnatprod.2c00624
Salmonella enterica subsp. enterica serovar Typhi Salmonella typhi MIC 0.05 ug.mL-1 10.1021/acs.jnatprod.2c00624
Salmonella enterica subsp. enterica serovar Typhimurium Salmonella typhimurium MIC 0.25 ug.mL-1 10.1021/acs.jnatprod.8b00321
Salmonella enterica subsp. enterica serovar Typhimurium Salmonella typhimurium MIC 1.0 ug.mL-1 10.1128/aac.00079-09
Serratia marcescens Serratia marcescens MIC 1.0 ug.mL-1 10.1021/jm00155a004
Shigella flexneri Shigella flexneri IZ 24.8 mm 10.1016/j.ejmech.2017.10.046
Shigella flexneri Shigella flexneri MIC 0.48 ug.mL-1 10.1016/j.ejmech.2017.10.046
Staphylococcus aureus Staphylococcus aureus Activity nan None 10.1021/acs.jnatprod.2c00621
Staphylococcus aureus Staphylococcus aureus DIZ nan None 10.1016/j.ejmech.2017.11.025
Staphylococcus aureus Staphylococcus aureus FIC 0.12 None 10.1021/acs.jnatprod.2c00621
Staphylococcus aureus Staphylococcus aureus MIC 0.03 ug.mL-1 10.1021/acs.jnatprod.2c00624
Staphylococcus aureus Staphylococcus aureus MIC 0.06 ug.mL-1 10.1021/acs.jnatprod.2c00621
Staphylococcus aureus Staphylococcus aureus MIC 0.06 ug.mL-1 10.1021/jm00155a004
Staphylococcus aureus Staphylococcus aureus MIC 0.07 ug.mL-1 10.1021/acs.jnatprod.2c00624
Staphylococcus aureus Staphylococcus aureus MIC 0.1 ug.mL-1 10.1016/j.bmc.2021.116580
Staphylococcus aureus Staphylococcus aureus MIC 0.13 ug.mL-1 10.1021/jm00155a004
Staphylococcus aureus Staphylococcus aureus MIC 0.21 ug.mL-1 10.1016/j.bmc.2021.116580
Staphylococcus aureus Staphylococcus aureus MIC 0.25 ug.mL-1 10.1016/j.bmcl.2006.09.007
Staphylococcus aureus Staphylococcus aureus MIC 0.25 ug.mL-1 10.1016/j.bmcl.2010.09.084
Staphylococcus aureus Staphylococcus aureus MIC 0.25 ug.mL-1 10.1021/jm00155a004
Staphylococcus aureus Staphylococcus aureus MIC 0.5 ug.mL-1 10.1016/j.bmcl.2010.09.084
Staphylococcus aureus Staphylococcus aureus MIC 0.5 ug.mL-1 10.1021/acs.jnatprod.1c00578
Staphylococcus aureus Staphylococcus aureus MIC 0.5 ug.mL-1 10.1021/acs.jnatprod.2c00621
Staphylococcus aureus Staphylococcus aureus MIC 0.5 ug.mL-1 10.1021/ml200202y
Staphylococcus aureus Staphylococcus aureus MIC 1.7 ug.mL-1 10.1016/j.bmc.2021.116580
Staphylococcus aureus Staphylococcus aureus MIC 20.0 ug.mL-1 10.1016/j.ejmech.2018.11.026
Staphylococcus aureus Staphylococcus aureus MIC 32.0 ug.mL-1 10.1016/j.bmcl.2010.09.084
Staphylococcus aureus Staphylococcus aureus MIC 32.0 ug.mL-1 10.1021/jm00155a004
Staphylococcus aureus Staphylococcus aureus MIC 64.0 ug.mL-1 10.1016/j.bmcl.2006.09.007
Staphylococcus aureus Staphylococcus aureus MIC 64.0 ug.mL-1 10.1016/j.bmcl.2010.09.084
Staphylococcus aureus Staphylococcus aureus MIC 64.0 ug.mL-1 10.1021/ml200202y
Staphylococcus aureus Staphylococcus aureus MIC 128.0 ug.mL-1 10.1016/j.bmcl.2006.09.007
Staphylococcus aureus Staphylococcus aureus MIC 128.0 ug.mL-1 10.1016/j.bmcl.2010.09.084
Staphylococcus aureus Staphylococcus aureus MIC 1000.0 nM 10.1021/acs.jmedchem.1c00614
Staphylococcus aureus Staphylococcus aureus MIC nan None 10.1021/acs.jnatprod.7b00496
Staphylococcus aureus Staphylococcus aureus MIC nan None 10.1021/acs.jnatprod.8b00321
Staphylococcus aureus Staphylococcus aureus MIC50 32.0 ug.mL-1 10.1021/ml200202y
Staphylococcus aureus Staphylococcus aureus MIC=>80 0.5 ug ml-1 10.1021/acs.jmedchem.1c01551
Staphylococcus aureus Staphylococcus aureus MIC90 32.0 ug.mL-1 10.1021/ml200202y
Staphylococcus capitis Staphylococcus capitis MIC 0.12 ug.mL-1 10.1016/j.bmcl.2010.09.084
Staphylococcus epidermidis Staphylococcus epidermidis DIZ nan None 10.1016/j.ejmech.2017.11.025
Staphylococcus epidermidis Staphylococcus epidermidis MIC 0.12 ug.mL-1 10.1016/j.bmcl.2010.09.084
Staphylococcus epidermidis Staphylococcus epidermidis MIC 16.0 ug.mL-1 10.1016/j.bmcl.2010.09.084
Staphylococcus epidermidis Staphylococcus epidermidis MIC 32.0 ug.mL-1 10.1016/j.bmcl.2010.09.084
Staphylococcus epidermidis Staphylococcus epidermidis MIC 64.0 ug.mL-1 10.1016/j.bmcl.2010.09.084
Staphylococcus epidermidis Staphylococcus epidermidis MIC 1000.0 nM 10.1021/acs.jmedchem.1c00614
Staphylococcus epidermidis Staphylococcus epidermidis MIC nan None 10.1021/acs.jnatprod.8b00321
Staphylococcus warneri Staphylococcus warneri MIC 0.12 ug.mL-1 10.1016/j.bmcl.2010.09.084
None ADMET C50 0.21 uM 10.1021/jm00385a015
None ADMET Kill at C50 85.0 % 10.1021/jm00385a015
None ADMET LD90 0.25 uM 10.1021/jm00385a015
None ADMET Uptake at C50 5.5 None 10.1021/jm00385a015
None Nucleic Acid Activity 0.42 /s 10.1038/nchembio.274
None Nucleic Acid Activity 5.0 % 10.1038/nchembio.274
None Nucleic Acid Activity 14.0 % 10.1038/nchembio.274
None Nucleic Acid Activity 67.2 % 10.1038/nchembio.274
None Nucleic Acid Frel 0.8 None 10.1016/j.bmcl.2005.02.007
None Phospholipidosis Phospholipidosis nan None 10.1021/mp100103e
None Phospholipidosis Phospholipidosis nan None 10.1080/15376510701857262
None Unchecked IZ 19.9 mm 10.1016/j.bmc.2020.115444
None Unchecked IZ 23.4 mm 10.1016/j.bmc.2020.115444
None Unchecked IZ 26.3 mm 10.1016/j.bmc.2020.115444
None Unchecked IZ nan None 10.1016/j.bmc.2020.115444
None Unchecked MIC 0.03 ug.mL-1 10.1016/j.bmc.2020.115444
None Unchecked MIC 0.24 ug.mL-1 10.1016/j.bmc.2020.115444
None Unchecked MIC 1.95 ug.mL-1 10.1016/j.bmc.2020.115444

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT002229 CC(=O)CC(=O)[CoA].CN[C@H](C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1>>CN[C@H](C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](N(C)C(=O)CC(C)=O)[C@H]3O)[C@H]2O)O1 enzymemap_31551
AKRT004383 CC(=O)[32S].CN[C@H](C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1>>CN[C@H](C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OCC(C)(O)C(N(C)C(C)=O)C3O)[C@H]2O)O1 None
AKRT004545 CC(=O)[CoA].CN[C@H](C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1>>CN[C@H](C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OCC(C)(O)C(N(C)C(C)=O)C3O)[C@H]2O)O1 enzymemap_31552
AKRT007169 CCC(=O)[CoA].CN[C@H](C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1>>CCC(=O)N(C)[C@@H]1[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@H]([C@@H](C)NC)CC[C@H]3N)[C@@H](N)C[C@H]2N)OC[C@]1(C)O enzymemap_32196
AKRT010879 CN[C@@H]1[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@H]([C@@H](C)N)CC[C@H]3N)[C@@H](N)C[C@H]2N)OC[C@]1(C)O.C[SAH]>>CN[C@H](C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1 RXN-13240
AKRT010919 CN[C@H](C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O>>CN[C@H](C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](NC)[C@H]3OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@H]2O)O1 enzymemap_48910
AKRT017774 NCC(=O)[CoA].CN[C@H](C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1>>CN[C@H](C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](N(C)C(=O)CN)[C@H]3O)[C@H]2O)O1 enzymemap_32187
AKRT022701 O=C(O)CC(=O)[CoA].CN[C@H](C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1>>CN[C@H](C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](N(C)C(=O)CC(=O)O)[C@H]3O)[C@H]2O)O1 enzymemap_32192